Three-way Nookie Rookie Needs Advice

Hey, Yana,

I’m a queer lady in my mid-20s and I’ve been with my boyfriend for about four years now. We’ve got an awesome hot and freaky sex life and we’re on the brink of our very first threesome with another girl. We’re both really excited that this is happening, but we’re wondering about threesome etiquette. How do we get things started? How do you be a good threesome host? What are some rules we should set?

— Threeway Nookie Rookie


Plans well-laid will get all three of you well laid! So, I’m glad to see that y’all are thinking about how to make your threesome safe and intentional rather than letting it occur willy-nilly, “by accident,” or in an otherwise alcohol-fueled happenstance manner. (Tip 1: Ditch the drinks.)

As an established couple, you’ve got some hosting responsibilities. First, have a frank talk with your boyfriend about boundaries and agreements. Remember, these can change and grow as you both evolve in your three-way practice — if it continues — so don’t widen your scope more than feels comfortable. As fellow sex educator Dawn Serra says, “It’s better to leave everyone wanting more than regretting that they didn’t do less.”

Some boundaries to consider: Penetrative sex acts tend to be precious between partners. Who can get penetrated by whom and where?

Safer sex agreements: Who’s on birth control? Do you have a truckload of condoms/gloves/dams so you can change them as many times as sex acts and partner-pairings change?



Is this a one-time thing or are you open to more sex with this particular person? … continue reading…


Husband Seeks Female-Friendly Sex Ed

Hi Yana,

My wife is interested in exploring her sexuality a little further — things she might be interested in trying, etc. — but is hoping to do so in a way that is female- and feminist-friendly. Do you have any suggestions for things she can do or read either individually or with me?

— Helpful Husband

Hello HH,

My favorite kind of husband is the one willing to lend a helping hand to his partner’s continued sexual exploration — especially when they’re flexible about their level of involvement!

Googling “sex” willy-nilly on the internet can get sticky to say the least. Before y’all surf the web, hit the books. Come As You Are by our very own local sexpert Emily Nagoski is the first thing to read. This is one of the most comprehensive, shame-reducing and normalizing books about sex I’ve read. Her helpful worksheets direct the reader through some great self-reflection and sexual explorations and can be done solo or with a partner (that’s you, HH!).

Other good readings include Mating in Captivity by my professional idol Esther Perel and O WOW: Discovering Your Ultimate Orgasm by Jenny Block.

Watching feminist porn either solo or with a partner is great sexploration fodder. Feminist porn isn’t that wam-bam-thank-you-whatever-your-name-was mainstream porn you find easily when you Google “porn.” Feminist porn is intentionally made for the non-male gaze, is often directed by women and queer people, features scenes co-created by the performers, and proudly displays real orgasms and consent practices. (Read my past column, Grass Fed Porn for more on feminist porn.)

Tristan Taormino directs great feminist-friendly sex educational porn she calls “expert guides” on topics that include female orgasms, the G-spot, oral sex, threesomes, and rough sex that blend smut and educational lecture for a real pleasurable learning experience.

Also, your truly humble sex columnist teaches a variety of workshops on topics such as the G-spot, kink, anal sex, non-monogamous relationships, and sex toys! You can find my upcoming workshops at

Sexual shame can be a heavy shroud to lift for a lot of people — especially women, queer people and other folks who have not been granted the same social permission to talk about and explore their sexuality and experiences of sexual pleasure that straight men have enjoyed…continue reading…


Babe Needs to Break Up

Dear Yana,

I want to break up with my boyfriend of a few years. As we both near 30 I’m getting clearer that he’s just not the guy for me.

But here’s the thing: We live together. We have a lease together. We share a car and a cat and just have so many logistical ties to each other that I’m having a really hard time figuring out a way to break up with him that makes everything as easy as possible.

I know that in the end we’re going to break up, but the timing just seems so hard. Do you have any suggestions for when or how I might find an opening to do it at the right time?

Babe Needs to Break Up

Dear BnB,

When it comes to ending relationships of course we’d all like to make the break as clean as possible, but the nature of break-ups is that, ultimately, something needs to end up broken. Cracks, fractures, and snaps are rarely successfully made without leaving behind at least one jagged edge. Putting effort into avoiding them completely is usually effort wasted. This doesn’t mean that there aren’t ways to break up well and lessen the damage, but coming to grips that things will be messy by design will save you some sweat.

I always find myself surprised at how, toward the end of a relationship, the things you loved most about your partner at the beginning can be the most toxic aspects of them at the end. Organized and driven becomes controlling and anal-retentive; Refreshing spontaneity becomes predictable irresponsibility; Sassy flirtation looks like a wandering eye, etc.

The first step to breaking up well is remembering that your partner doesn’t need to be the undesirable bad guy in order to justify your decision to break up. Break-ups are allowed without projection…continue reading…


Live *WEBINAR*: The G-Spot & Vaginal Ejaculation! // July 21st

LIVE WEBINAR: The G-Spot & Vaginal Ejaculation || Thu, Jul 21, 2016 7:30 PM – 9:00 PM Eastern Standard Time {New York} || $15 per seat || 18+ || register & purchase tickets here! 

Workshop Description: This webinar busts myths about the G-Spot & Vaginal Ejaculation (it doesn’t exist! it’s the best orgasm ever! OMG PEE!!) and leaves participants with tools and tricks to learn the vaginal ejaculation trade.

This webinar lets participants tune in as I present live how to choose and utilize sex toys for G-Spot stimulation {non-explicit demonstration only}, present lube 11401179_771921860468_9034498346160463912_ndemos, and teach sexual anatomy 101 to teach about where this sneaky spot is, how to stimulate it (on yourself & others) and how to work towards the epic squirt.

Taking a holistic approach to sexual pleasure, this webinar also offers information about the clitoris, the power of our sexual context, and how to talk to partners about our pleasure. Open, honest and full of humor, this webinar reminds participants to have fun as they explore the sexual pleasure packed in this little spot.

Webinar will include time for participant questions and attendees will log off with helpful handouts and the password to my personal online selection of resources to dig into when the webinar is over.

|| Register & purchase tickets here !! || 

Read more about Yana & her work here on her About Me page.


Double the Pleasure w/Synced Orgasms

Hi Yana,

I recently attended one of your workshops about the G-spot and it worked! My partner and I went home that night and I squirted. But it’s so strange because when I squirt it doesn’t happen as I climax. It isn’t like a climactic orgasm. It just feels crazy good and then I squirt. We were wondering if we could time it so that I could have the clitoral climax at the same time that I squirt?

— Star Squirting Student

Dear SSS,

Holy Star Student status! Plenty of folks report success with their newly learned sexpertise from my workshops, but OMG-spot, rarely do people go straight home and start squirting all over the place the very same night. As I say in my workshops, I can spend hours giving you information, but it’s up to you to have the bravery to utilize and communicate that information to your IMG_6401partners — so good on you.

I’m so glad you bring this up as in my G-spot workshops, I aim to address many myths barring us from great G-spot explorations and pleasures including:

That it doesn’t exist. (Hi, it does — I don’t just go around teaching workshops about unicorns);

That female ejaculation is pee. (I’m a grown woman, I think I know the difference between peeing my bed and having an orgasm);

And finally, that a G-spot orgasm is the orgasm of all orgasms.

You are living, breathing, squirting proof, SSS, that this simply isn’t true for everyone. While a G-spot orgasm feels more like an internal, pleasurable release, a clitoral orgasm can often feel more surface, intense and, well, climactic.

If we look at where these two pleasurable spots are located and how they’re stimulated, this makes a lot of sense...continue reading…

LIVE WEBINAR: The G-Spot & Vaginal Ejaculation || Thu, Jul 21, 2016 7:30 PM – 9:00 PM Eastern Standard Time {New York} || $15 per seat || 18+ || details & tickets here!


Is Being Basic in Bed a Bad Thing?

Dear Yana,

Recently my partner and I have talked about sexual exploration- or lack thereof – in our relationship. I don’t have any fetishes or kinks or fantasies. At least, I don’t think I do. I’ve never even owned a sex toy. Not that this is a problem, but I sense from my partner that he wishes otherwise.

He finds my “vanilla” preference for the sexual experience “interesting”- his words. Read: boring. Now I’m questioning if I’m suppressing a desire to expand my sexual horizons or if I really just don’t get off from a sexual experience separated from reality. I guess the only way to know is to try exploring or I’ll never know, but I wanted to hear what you have to say and what you recommend for proceeding.


Basic in Bed


Dear BinB –

There are a few reasons why I tend to use the term “pleasure-positive” to describe my work rather than “sex-positive” (though I’m truly a mix of both): on the one hand the “sex-positive” movement has been really, well – positive! Sex-positivity counters slut-shaming, casts sex as a natural, albeit complicated part of our lives rather than inherently risky or negative, and has opened many doors for people that had been previously barricaded by shame, stigma, and repressive social norms.

Pleasure-positivity is sex-positive. However, it’s more heavily focused on what brings us pleasure as unique individuals. The reason I bring this up, BinB, is that while sex-positivity may help your partner feel empowered and excited about his kinks and fetishes, it may feel simultaneously disempowering to you as someone who finds pleasure in what feels, as you describe as, based in reality and/or vanilla.

Though your sexual pleasure may present as vanilla in comparison to his triple-chocolate chip with whipped cream, cherries, sprinkles, and handcuffs, your unique experience of sexual pleasure is just as valid as his. For some, intimate pleasure has nothing to do with sex at all!

Kate McCombs, MPH, my sex education colleague, states so gracefully; “There’s a huge variety of what’s ‘normal’ when it comes to sexual desire. Often people with lower desire for sex feel broken or weird. If that’s you, you’re not alone. In my opinion, prude-shaming is just as problematic as slut-shaming. As I like to say ‘I’m sex-positive – not sex-mandatory’”. Similarly, being kink- or fetish-positive doesn’t mandate it be a part of your sexual experience.

Of course, there are always two sides to every coin and endless sides to the complex shapes our sexual and romantic lives can take. If you would like to explore some other sides, there are a couple places to dig into.

You seem overwhelmed at the idea of exploring this wide realm of other-than-vanilla sex – understandable! A simple Googling of “kinky sex” can lead you into quite the overstimulating rabbithole, to say the least. Sexual exploration can be an extremely personal process and may look like fantasizing about something new for a few minutes while you masturbate, taking a vibrator for a spin, or diving headfirst into the porn pool. Some feel safe and comfortable exploring with their partners present and others need some solo space to process, feel awkward, or to just throw that new vibrator on the floor and swear them off for life.

For others, sexual exploration can mean a deeper process of unpacking what makes us feel hesitant about moving beyond the sex we know or the sex we’ve been granted social permission to have. I’m particularly interested in what you might discover by thinking about what makes reality-based sex feel good and safe to you.

Your partner has a responsibility to not pressure you into any kind of sex that you don’t feel consensually and enthusiastically YES about and also if you do decide to explore new sexual things with him, to be patient and supportive if certain things just don’t float your bangin’ boat.

Some suggested reading includes When Your Sex Drives Don’t Match by Sandra Pertot, Come As You Are by Emily Nagoski, and Mating in Captivity by Esther Perel.

No matter what, keep in mind this mantra by sex writer & educator Emily Nagoski, PhD: “Pleasure is the measure”; not your kink-o-meter, not the flavor of your freakiness, but your genuine pleasure.

This sex column appears in print on the back page of The Valley Advocate every week!

Email me your sex & relationship questions to be anonymously answered in the V-Spot!